Diastereoselective episulfidation of strained cyclic alkenes by a thiophene endoperoxide versus epoxidation by dimethyldioxirane

W Adam, B Fröhling, K Peters…

Index: Adam, Waldemar Journal of the American Chemical Society, 1998 , vol. 120, # 35 p. 8914 - 8919

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Citation Number: 18

Abstract

Thiophene endoperoxide 2, which was prepared by photooxygenation of thiophene 1, transfers a sulfur atom (up to 92%) to strained cycloalkenes to form thiiranes when thermolyzed in their presence. The diastereomeric pair cis/trans-cyclooctene (5b) reacted stereoselectively, which speaks for a concerted process rather than open dipolar and/or diradical intermediates. The set of chiral cyclooctenols 5c-e was also investigated, and the ...